The chemical name of prasugrel is 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate and is shown below.
Its molecular formula is C20H20FNO3S, and its molecular weight is 373.44.
Prasugrel is an oral platelet inhibitor and an anticlotting drug. It was originally developed for patients suffering from acute coronary syndrome who need percutaneous coronary intervention, including patients who need stent placement. Research results show that prasugrel could reduce the death resulting from nonfatal heart disease and stroke more effectively than clopidogrel, and decrease the stent thrombosis risk.
Eli Lilly filed a patent application US 2008176893) relating to prasugrel hydrochloride in 2006, in which it claimed a formulation and method of administration. A film-coated, diamond-shaped tablet of 5 or 10 mg prasugrel hydrochloride (prasugrel, Efient) is currently available in Europe and the USA. A single loading dosage of 60 mg is typically followed by maintenance doses of 10 mg per day. At the same time, 75-325 mg aspirin is co-administrated every day. Prasugrel hydrochloride is slightly soluble at pH 1-4, very slightly soluble in pH 5 and insoluble in pH 6-7. The hydrochloride acid addition salt has higher bioavailability than its free base form at higher gastric pH conditions. According to related reports from FDA-review, the bioavailability of prasugrel hydrochloride or its free base form is about equal when the drugs are administrated alone. When prasugrel hydrochloride or its free base form is administrated together with PPI or H2 receptor antagonists (resulting in higher pH conditions), the bioavailability of the free base form is lower than the hydrochloride acid addition salt form. According to this disparity in solubility of prasugrel hydrochloride and its free base, it is desirable to improve the bioavailability of the free base form to overcome the solubility difficulties at different pH conditions.